A Cuban American’s story proves dreams really can come true
When Olga Ramudo was a stay-at-home mom in Miami, she never imagined she’d one day lead one of the largest Hispanic and women-owned travel companies in Florida. But that’s exactly what she did, turning her love for organizing group trips into a thriving business that has now become a global powerhouse.
How planning family ski trips turned into a thriving company
In the late 1980s, Olga and her sister started planning ski trips with other families from their kids’ school. They started with 30 people, but soon grew to 100, and eventually, they chartered entire planes filled with 500 Cubans headed to Vail, Colorado.
Realizing they were doing all this work for free, they became independent agents of a small travel company. However, the demand kept growing with friends asking them to handle all their corporate travels. Eventually, in 1989, they ended up launching Express Travel.
Initially, the company handled family vacations. However, they soon expanded to offer much more. Express Travel was soon handling corporate travel, leisure trips, study abroad, and meetings and incentives.
In 2023, they caught the eye of Gray Dawes, a UK-based travel management firm. Though Olga wasn’t planning to sell, she knew it was the right move to secure the future of the company she and her partners had built from scratch.
Today, Express Travel is the U.S. headquarters for Gray Dawes, with offices in several countries around the globe, including the UK, Netherlands, Australia, and soon New Zealand.
Cuban-American roots
Olga Ramudo credits her Cuban American roots for shaping her values and vision. Growing up, she learned the importance of family and culture.
She believes Hispanics have a special way of traveling (always together), no matter the destination. That spirit has become one of the core values of Express Travel. “When Hispanics travel, it is rarely about the destination. Traveling is about togetherness and sharing experiences,” Olga explained. “You know, there have been many ski trips where most people don’t ski, but everyone still shows up in matching outfits just to be part of the fun. That sense of belonging and celebration has always been a central part of Express Travel since the beginning.”
She’s also deeply committed to preserving the legacy of Cubans through FACE (Facts about Cuban Exiles), where she is a board member. Recently she was featured in the Oral History project which recorded and celebrated the journey of several prominent Cuban Americans. This project is so important, that it received the support of the Knight Foundation..
Olga Ramudo came to Miami from Cuba in 1959, just two months after Castro took power. “My father immediately recognized communism and decided to leave his current life in Cuba behind,” Olga said. “Our family lived for three months in the De Lido Hotel, which is now the Ritz-Carlton; soon after, we had to look for a house since dad sold everything he owned and had all furniture, clothes, cars, artwork, etc. loaded in containers and shipped to Key West. Afterwards he started doing what he did in Cuba, build homes. He built one for the family, enrolled in U.M to study English, enrolled us kids in St. Theresa school, and started over”.
For Olga Ramudo, being involved in this project honors that legacy. Though she has spent most of her life in the U.S., she feels equally Cuban and American. Her parents passed down their culture and pride, which she has also shared with her children. “I have this deep connection to heritage, and I have passed it on to my children. We do things like gathering for lechón and croquetas. It makes this initiative especially meaningful.”
The challenges
Every business faces its share of challenges along the way, and Olga’s journey is no exception. Initially, banks did not take her seriously, so acquiring a loan proved to be difficult. But thanks to Willie Alexander who was a director at Hamilton Bank at the time and knew her and her partners personally, they were able to secure a $30,000 loan.
Later, the rise of the internet posed another major hurdle, as people started booking travel online. To stay competitive, they focused on offering expertise and personalized service. Like using an accountant or attorney instead of doing it yourself, clients trusted them to get the best options. That commitment to knowledge and care kept Express Travel growing even in the digital age.
Legacy for the future
Olga Ramudo advices young Cuban American women to always speak up, be themselves, and not be afraid to try something new.
She hopes her story shows that dreams really can come true if you try hard enough. As she says, “Sometimes you don’t know exactly how you’re going to do something, but you figure it out along the way. So, stay strong, speak up, be yourself, and don’t be afraid to try something new.”
As a Cuban American, Olga Ramudo also wants to honor and share the pride in how much Cuban Americans have contributed to the country that she loves deeply.
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